U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C9H15NO2
Molecular Weight 169.2209
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACECLIDINE

SMILES

CC(=O)OC1CN2CCC1CC2

InChI

InChIKey=WRJPSSPFHGNBMG-UHFFFAOYSA-N
InChI=1S/C9H15NO2/c1-7(11)12-9-6-10-4-2-8(9)3-5-10/h8-9H,2-6H2,1H3

HIDE SMILES / InChI

Description
Curator's Comment: Description was created using several sources including: https://www.ncbi.nlm.nih.gov/pubmed/16229863 | https://www.ncbi.nlm.nih.gov/pubmed/12579779 | https://www.ncbi.nlm.nih.gov/pubmed/10845594

Aceclidine is a parasympathomimetic agent used in the treatment of open-angle glaucoma as topical eye drop solution. It is as a muscarinic acetylcholine receptor agonist with weak anticholinesterase activity. Acting directly on the motor end-plate (cholinergic nerve endings) it decreases intraocular pressure and mediates the contraction of iris muscle. Aceclidine increased outflow facility in human eyes in vitro by a direct stimulation of the outflow tissues in the absence of an intact ciliary muscle. This effect was biphasic, occurring at concentrations of 10 uM and lower with no effect at higher concentrations. Passed numerous clinical trials in Russia, France, Italy and other countries and was widely used in Europe but never been in clinical use in USA.

CNS Activity

Curator's Comment: Known to be CNS penetrant in mouse; rats. Human data not available

Originator

Curator's Comment: Aceclidine was first prepared in 1960

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Glaunorm

Approved Use

Glaucoma, in its different clinical forms

Launch Date

1969
PubMed

PubMed

TitleDatePubMed
[The selectivity of the action of muscarinic agonists in vivo].
1994 Mar-Apr
Pharmacological management of night vision disturbances after refractive surgery Results of a randomized clinical trial.
2005 Sep
Aceclidine and pilocarpine interact differently with muscarinic receptor in isolated rabbit iris muscle.
2006 Feb 28
Aceclidine, brimonidine tartrate, and dapiprazole: comparison of miotic effect and tolerability under different lighting conditions.
2009 Jan
Effectiveness of daily use of brimonidine as antimydriatic agent.
2009 Oct
Role of cholinergic and cytokine regulation of T cell function in stimulation and inhibition of immune reactions in intoxication by organophosphorus compounds in different doses.
2009 Sep
Patents

Sample Use Guides

Instill 2 drops of Glaunorm (2% aceclidine hydrochloride solution) into the conjunctival sac every 8 hours following the doctor's prescription
Route of Administration: Topical
Human eyes were dissected and perfused. A steady state baseline facility was established for 90 minutes, after which up to four sequential concentrations ranging from 1 nM to 10 mM of aceclidine, were added to the perfusion medium. Outflow facility increased from baseline facility in eyes treated with aceclidine at lower concentrations (1 nM to 1 uM) but remained unchanged at higher concentrations.
Name Type Language
ACECLIDINE
INN   MART.   USAN   WHO-DD  
INN   USAN  
Official Name English
Aceclidine [WHO-DD]
Common Name English
NSC-657843
Code English
3-Quinuclidinol acetate (ester)
Common Name English
ACECLIDINE [USAN]
Common Name English
3-QUINUCLIDINOL DL-FORM ACETATE (ESTER) [MI]
Common Name English
3-ACETOXYQUINUCLIDINE
Systematic Name English
NSC-758239
Code English
1-AZABICYCLO(2.2.2)OCTAN-3-OL, ACETATE (ESTER)
Common Name English
ACECLIDINE [MART.]
Common Name English
aceclidine [INN]
Common Name English
Classification Tree Code System Code
WHO-ATC S01EB08
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
NCI_THESAURUS C47796
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
WHO-ATC S01EB58
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
WHO-VATC QS01EB08
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
WHO-VATC QS01EB58
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
Code System Code Type Description
CAS
827-61-2
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PRIMARY
PUBCHEM
1979
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PRIMARY
EVMPD
SUB05199MIG
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PRIMARY
EPA CompTox
DTXSID2045658
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PRIMARY
MESH
C084650
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FDA UNII
0578K3ELIO
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NSC
657843
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MERCK INDEX
m9469
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PRIMARY Merck Index
NCI_THESAURUS
C81044
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DRUG BANK
DB13262
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PRIMARY
NSC
758239
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PRIMARY
WIKIPEDIA
Aceclidine
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PRIMARY
ChEMBL
CHEMBL20835
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PRIMARY
ECHA (EC/EINECS)
212-574-1
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DRUG CENTRAL
4314
Created by admin on Fri Dec 15 16:35:08 GMT 2023 , Edited by admin on Fri Dec 15 16:35:08 GMT 2023
PRIMARY
INN
1367
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PRIMARY
SMS_ID
100000087890
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PRIMARY